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What's up, guys? Welcome back to Build. And today we're going to talk about what I've learned hiring an executive team twice. So this is very top of mind for me because this is, I want to say, the, I don't know, second or third time in my career that I've hired a full executive team for my business. And the first time I did it, it was very nerve wracking. It was like just trying to figure out what way was up. Everyone would tell you what executives are supposed to look like and what they do and the difference in hiring them. But then doing it is another thing. And you really have like a 50, 50 shot of it working out or not with an executive. And I honestly think even with a lot of experience, it still kind of goes that way because until somebody gets in there and you're working together, it's just really hard to know how it's going to work for a long period of time. And I'm reminded of this because right now with acquisition.com my team knows that my focus this quarter has been expanded, expanding our leadership capacity. You know, we surpassed and are well on our way to multiple nine figures in 2026. And in terms of revenue, not value. And that has happened very quickly. And doing that, what I recognize is like, we have just not been able to keep up from a leadership capacity standpoint. So not only do I want to make sure that we can handle everything happening now, but we can build the capacity for the Runway where we want to go in 2026-2028. And so I spent all of my time on calls with recruiters. First selecting recruiters, then selecting what do we do ourselves, then talking to candidates, flying candidates out. Like, I have just been completely externally facing. I have been doing way less content. I have been doing way less one on ones. I even told my team, listen, if you need a one on one, just ask for it. I don't even have time because I'm doing so many interviews on top of other things that I cannot get rid of as CEO of the company. And that is something I've never done before. But I just realized that this is our bottleneck and I wanted to go full force at it. So that being said, as I'm going through this process, one, it is so much easier than the first couple times I've done it. And two, there's just a lot more that I've realized and I think especially in working with my team and educating them on what an executive does, I've realized there's A lot of gaps in what people think an executive team looks like versus what an executive team actually looks like. And if you're wondering, are you at the point where you should hire an executive team in your business, I want to describe that to you first so you can kind of understand if this is something on apply now or apply later. I think that there's a moment for everybody when you are growing your company where you realize that essentially the company has outgrown you. And it's not because it outgrew your vision or it outgrew your hard work or your ambition. It's you. It's like you are running everything you might be running. You're making decisions for media people, operations, finance, IT, tech, and every decision that matters really comes back to you. And when you're small, that works well because there's not as many decisions. And if you make the wrong decision, it's easy to pivot when you're small, I totally get that. But once you have the Titanic, it's like steering a rowboat versus steering the Titanic. Very different things. If you don't steer the Titanic in time, you hit a iceberg, right? And so once your business becomes like the Titanic, you start noticing things, right? Which is one, I would say, like the signs that you probably are at the point where you need an executive team, or even just a leadership team, mind you. You have to consider revenue and size of the business. One, strategic conversations get shorter, not because you're getting more efficient at having them, but because you don't have time. You don't have time to think about strategy, don't time to talk about strategy, right? So you might talk about expanding into this new vertical for 15 minutes. Then somebody knocks on the door, tells you about something, and then, oh, shit, I got to go do this thing. For the next four hours. The work isn't getting worse, but it's getting smaller. And I think that's at the point where you realize, like, if you want to go from tens of millions or hundreds of millions to hundreds of millions or billions, you can't just hire more people to do stuff. You have to hire people to think about stuff. You want to hire people who don't need you to tell them what to do. Okay, a lot of people think, well, I can train them up. I can do this. Let me just put it to you this way. You know, something I had to come to the unfortunate realization of is like, you know, as a CEO, when there are, you know, I'm building out a C suite with, you know, Eight people in it because of the type of company we have. The. Yeah, I actually don't have time to develop anybody. I have time to give them feedback. I don't have time to teach them how to do their job very different. Providing feedback on behaviors and context of the business is very different than telling them how to be a cto, cfo, coo, cpo, whatever it might be, right? That takes a lot more time. And unfortunately, when your business gets to a certain point, you just. You actually just don't have the time to train people on things like that and how to do their job. And so instead, you want to find people who can take entire chunks of your business off your plate, not even just by executing the vision that you have, but by making it even better. The number one thing that I learned in hiring executives in the past and in the present is it is not like hiring employees, okay? It is more like choosing a partner. And honestly, I do call most of my direct reports my partners. I don't call them like, oh, my employees. Like, I just actually don't really love them using that word. I use it for the sake of explaining things, but I don't really use it personally. And when you get those people in, they don't work for you. They actually change the trajectory of what you're building because they have more capability and capacity than you do. And it's not just that they are doers. It's that they are thinkers, they are strategic. And a lot of people are very good at hiring doers. Okay? You know what I'm talking about. It's like they're hungry, they're fast, they'll run through a wall. They see a problem, they fix it. You give them problems, they crush it. Now, I'm not saying executive can't have that element to them. And I actually think it's a very much a skill you want for them to be able to do that when needed. However you want them to play a different game. They're not just there to take tasks off your plate. They're here to change the questions that you are asking. They're there to change the frame in which you see the business or the function. And if you've never hired one before, like I had not, you know, seven years ago, you actually don't know what to look for. Because the qualities that make someone a fantastic executor are not the same qualities that make someone a great executive. And I wish somebody had told me that, because sometimes what you'll realize is that you hire someone and you're like, well, they're so good at doing this thing, and they seem like a nice person. Like, I'm sure they can be a leader. And then you realize that instead of you being the bottleneck, they become the bottleneck, and you don't want that either. And I think that's a really big piece. I want to explain five things that I want to share with you guys that I think are, like, the biggest lessons that I've learned in hiring executives. And I want to give these to you so you can use them either now or in the future. So the first one is that they make you think bigger, not just work less. Okay. The first time I hired an executive, I really got this wrong. I got it wrong because I was hiring for capacity, and I needed someone to manage a function that was taking up a lot of my time. It was my tech function. And so I found somebody that was, like, good at managing that function, which it's like, okay, great, problem solved, right? No, because I realized three months in, I had traded one problem for another. Instead of doing the work myself, I was now managing somebody doing the work who was also the out the bottom line. And so that's where you have to understand, like, the right executive isn't just going to lighten the load. They are going to sharpen your thinking, and they are going to strategically build out the function. You know that you're in the right room. And with the right executive, when you walk into the meeting with a problem and you walk out with either a completely different idea of the solution or a different question. For example, I might walk into a marketing meeting and ask the marketing executive, like, how do we convert this campaign? How do we get it to convert better? And they might say, well, before we optimize the campaign, why are we targeting this segment at all? Is this even the right market that we're trying to build? And suddenly I'm like, oh, shit, oh. And then what you realize is this is very small nuance, which is they're not talking about tactics, they're talking about strategy. And that's the difference. Executors, they need direction. Executives need context. So you have to give them the why, and they will figure out a better what. The test of this, in my opinion, when you are interviewing people, is if those conversations leave you thinking bigger, do you think bigger by speaking to this person? I gave somebody on my team feedback the other day. They said, hey, I'm interested in this executive role. Because when I told my team I'm hiring for executives, I Said like, listen, if you want to make an argument for why you should be one, let me know. And this is one of the things I flagged with them is I said, actually, every time I talk to you, I don't leave thinking bigger. I actually leave thinking about a million details that I don't even want to think about, dude. And it was a great conversation because the person was like, ah, fuck. Okay, yeah, that's a good point. I don't have that. And I was like, yeah. And I, I can't get pulled into the weeds. Neither can an executive at this point. The business is too big for it. But a lot of people just see what has made them successful up to this point. They assume, okay, well, more of that gets me to the next level, but it's just not. And I would say that one of the biggest leaps that you make is actually the one where you go from having somebody as an individual contributor, even a high level one in a leadership position, to a true executive. The second thing that you want to keep into consideration when you're hiring executives is that you're not just hiring, you're also being hired. Okay, so this one, like with my head for a while. But when you're used to hiring people, you are used to being the one evaluating in all the conversations. So you're used to asking the questions they're answering. You decide, are they good enough for the job. When you are hiring executives, especially very good ones, that dynamic is going to flip. And if anything, it's at least 50, 50, okay? These people, if they're good, right? If you're looking at quality ones, they, they have options, lots of options. They probably already built something impressive somewhere else. They might have had their own business. So they're not just asking, is this job good for me? They're asking, is this company worth my next chapter of my life? I will tell you this, if you cannot paint the vision of the company for them, it is going to be a very tough road. I remember one interview, I was walking through the role with somebody and halfway through the guy stopped me and he was like, this sounds amazing, but I don't really give a fuck about the role. I just wanna know where you're trying to take this company. And I was like, oh, shit. And I realized, I was like, oh. Because that day, specifically this is a few weeks ago, I had gone from a bunch of tactical interviews with people who are coming in to do things into an executive interview. And I had totally missed what I typically do for the first 20 minutes of an intro with an executive, which is explaining the mission and the vision. And what that means is, what you have to understand is they're not just picking a job, they're picking a mission. They're picking a future, a story that they want to be a part of and tell as a part of their career. Here's the test for if you know if this person has that mentality, if they don't ask you deep questions about where the company is going, they are probably not the right fit. Because the best executives care more about the future than the title. Now, the third lesson is all executives multiply themselves. When you hire an executive, you're not just hiring one person. You are hiring every person that they are going to hire everybody that they're going to train, everyone who's going to model their behavior. So think about like this, right? If they're impatient, your department always feels rushed. If they're political, your culture starts. Starts to feel gross and corporate. If they're mediocre, your standards start to drift and they start to degrade. So they don't just manage people, they multiply themselves in the organization. So before I hire someone on the executive level, I ask myself a few questions. Okay? One, will people on their team look up to them, not just respect them, but actually want to be more like them? Will they be loyal to this person? Will they create a team? Or will they create a team of loyal followers? Two, would I feel proud to put them on stage in front of our clients, to put them in a call with our partners? Would I want them representing the company when I'm not in the room? Executives have to be able to represent you when you are not there. And then three, is this someone I genuinely want to have dinner with? Like someone I'd want to keep learning from? I know it sounds silly, but you're going to spend so much time with your executives, and it is talking about what you're thinking about and strategy. And if you do not like being around them, that is just gonna be difficult. I don't care what people say. I think it's bullshit. You have to like your executive team. And then the last one, which I think cuts through a lot of noise that I ask myself, is, if I had kids, would I want them to work for this person? And now why do I ask that? Because it reveals what is more important in this role than anything, which is character. Character scales. And if you have competence but you don't have character, that is just like a time bomb waiting to go off. The fourth lesson is that the best executives build themselves out of a job. I know it sounds kind of backwards, but it is absolutely true. Like the best executives are not indispensable. They actually make themselves unnecessary. So they don't hoard information, they don't bottleneck decisions, they don't create a world where everything has to run through them. They build systems, processes, frameworks that make it easier for everybody to win. And over time, that keeps things running even when they're not in the room. So I'll give you an example. I hired someone in my last business to run operations. Within six months she had built out entire decision making framework for the team. Like not rules, but a framework. So now when somebody has a question, they don't have to wait for a meeting, they can just think through it themselves. That sounds so silly and nuanced, but the cool thing is that they taught the framework to their team and then those people taught it to other teams and to new hires. That is what great executives do. They don't just solve problems, they make sure those problems don't come up again. The test here is to ask them, what's a system that you built that's still running today without you? And if they can't answer that, they're probably not a builder, they're probably just a manager. Lastly is lesson five. They have to fit your team. There is no such thing as a universally great executive. There are only great executives who are great for your stage of your company. So like a corporate executive who thrives in a Fortune 500 company, they might drown in a startup or in a small company and a really scrappy executive who crushed it in a 20 person company might be completely lost in a 500 person organization. And so the question is not are they impressive? The question is, can they thrive in the specific business we're in right now and help us bridge to what's next? I made this mistake early. I hired in my last company a CTO with an incredible resume. Huge company, big title. It was Google and Apple. And he was just not a fit. I saw it in the first three days. He hated it, I hated it. And it wasn't because he wasn't talented. It was because we didn't have the structure that he needed to succeed. And so now I ask myself a different question, which is like what size of team and revenue range do you work best in and why? Because executives who know themselves will tell you and the ones who don't, they will tell you that they can do anything. And that is when I'm like pass. Pass. Because not everyone can do everything. What I've learned from hiring executive teams, it is not about offloading the work. It's about upgrading your thinking. And it's about surrounding yourself with people who make you better, who challenge you, who stretch you and force you to ask bigger questions. And when that happens and you get it right, you will stop being the person with all the answers, and you will start being the person with the best questions. And that is a cool moment, because that is when you go from running the business to actually growing it.